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$490,000
3 Beds ⋅ 2 Baths ⋅ Oakland Shores SubDv. ⋅ 32751 Zip Code
Beautiful Mid-Century Modern in Maitland! Sylish 3-bed, 2-bath, single-story home with 2-car garage + office on a quiet, tree-lined street. Features include vaulted ceilings, hardwood floors (no carpet), updated kitchen and baths, and a wood-burning fireplace. Enjoy a sunny Florida Room overlooking the fully fenced backyard. Upgrades include NEW energy-efficient windows, built-in closets, smart lighting and cameras, and fresh, modern paint colors. The chef’s kitchen offers stainless appliances, farmhouse sink, and ample cabinetry. Perfect for entertaining—dine al fresco on the large patio under shade trees or gather inside the Florida Room. No HOA. Just minutes from Maitland City Centre, the 414 for easy travel and 10 minutes to Park Avenue. Call today for your private showing.

515 W Faith Terrace, Maitland
$455,000
3 Beds ⋅ 2 Baths ⋅ Greenwood Gardens Sec 01 SubDv. ⋅ 32751 Zip Code
Step into this delightful 3-bedroom, 2-bath split plan home, perfectly nestled in one of Maitland's best-kept secret neighborhoods. As you approach, a spacious front porch welcomes you—the perfect spot to enjoy your morning coffee or an evening unwind. Inside, you'll find a home that's been thoughtfully updated and is ready for its new owners. Freshly painted walls and brand-new bedroom carpets create a clean, inviting canvas. The main living areas feature beautiful saltillo tile, a stylish and durable foundation just waiting for your personal touch. The home's open floor plan is anchored by a kitchen that was remodeled in 2013, complete with a cozy eating area that's ideal for casual meals or gatherings. The spacious living room is the heart of the home, boasting vaulted ceilings, with two skylights, and a charming wood-burning fireplace that adds warmth and character. One of the standout features is the incredible backyard, a true entertainer's paradise. A 500-square-foot patio with a wooden pergola provides a fantastic space for relaxing or hosting get-togethers. The generously sized, fully fenced yard offers plenty of room for outdoor fun and games. Plus, a versatile outdoor shed is ready to be transformed into your dream workshop, a tranquil "he/she shed," or even an outdoor kitchen. This home offers the perfect balance of privacy and convenience. Key updates include a new roof (2022) and a complete repipe (2016), giving you peace of mind. Its prime location puts you just minutes from local favorites like the Enzian theater, Publix, Kappy's Subs, the Sunrail station, and the vibrant dining and shopping scene of Winter Park and Lake Lily. Ready to see this Maitland gem for yourself? Let me know if you'd like to schedule a showing!

741 Robinhood Drive, Maitland
$475,000
4 Beds ⋅ 3 Baths ⋅ Maitland Village SubDv. ⋅ 32751 Zip Code
Charming and Spacious Townhome in Maitland! Welcome to 1938 Michael Tiago a beautifully maintained 4-bedroom, 2.5 bathroom home located in the desirable Maitland Village Community with a POND VIEW and END UNIT. This stunning property offers a perfect blend of classic charm and modern convenience, making it an ideal place to call home. As you approach this inviting residence, you’ll notice the lush landscaping and curb appeal that instantly sets the tone for what’s inside. Step into the spacious living area, where natural light pours in through large windows, creating a warm and inviting atmosphere. The open-concept floor plan seamlessly flows into the dining area and kitchen, making this space perfect for both everyday living and entertaining guests. Crown molding enhances the rooms adding just that right touch! Custom Plantation Shutters adorn all the windows downstairs & upstairs. The kitchen is a chef's dream, featuring stainless steel appliances, granite countertops, and ample cabinet space for all your culinary needs. A walk in panty is another feature of the kitchen. Whether you're preparing a weeknight meal or hosting a dinner party, this kitchen will exceed your expectations. The primary suite is generously sized and offers a peaceful retreat, complete with a private en-suite bathroom featuring a dual vanity, soaking tub, and a separate walk-in shower. Two additional well-appointed bedrooms provide plenty of space for family. The fourth bedroom featuring French Doors is located downsttairs...it can also be used as an office if needed. The Loft upstairs is light & bright and would make a great office or home school area. The Tile Roof brings long lasting peace of mind. This is an End Unit which allows for more light to filter thru from outside. Hot Water Heater is new. New Stainless Steel Dishwasher & Disposal are being installed. HOA fees cover exterior maintenance, 500 Mbps internet, 250 channel cable, water, sewer, trash, lawn care, sprinklers, streetlights, community pool, clubhouse, gate access and management services. Your low HOA fee takes care of all the yard work so you can enjoy the Community Pool. This makes living here "totally carefree living at its best". Other highlights include tile & engineered wood flooring throughout downstairs, a covered porch with a pond view, no neighbor on one side and a 2-car garage that has 2-car EV-ready. Located just minutes from shopping, dining, and major roadways, this home offers the convenience of being close to everything while providing a quiet, serene neighborhood feel. Don't miss your chance to own this charming Maitland home. Schedule a showing today and make 1938 Michael Tioga your new address!

1938 Michael Tiago Court, Maitland
$647,000
3 Beds ⋅ 3 Baths ⋅ Greenwood Gardens Sec 02 Rep 01 SubDv. ⋅ 32751 Zip Code
One or more photo(s) has been virtually staged. Step inside this home from anywhere! To experience a fully immersive walk-through of this home click on the Video or Virtual Tour button on this page. Welcome to one of Maitland’s best-kept secrets! Tucked away in a peaceful, no-through street with Maitland Park right across the way, this charming corner-lot home offers the perfect balance of privacy, comfort, and convenience. From your doorstep, you can walk to favorite restaurants, coffee shops, and the Brightline station, while Lake Lily Farmers Market, Downtown Maitland, and vibrant Winter Park are only minutes away. Step inside and you’ll be greeted by a spacious open layout, filled with natural light and designed for easy living. Wood-look tile flows seamlessly throughout, offering both style and low maintenance. The large living room centers around a cozy wood-burning fireplace, creating the perfect gathering spot for family and friends. The kitchen is a true standout with warm wood cabinetry, granite countertops, stainless steel appliances, and a sleek tile backsplash. Just off the kitchen, an enormous bonus room adds incredible flexibility—use it as a second living area, playroom, home gym, theater, or anything your lifestyle requires. The split floor plan ensures privacy for the oversized primary suite, which includes ample space for a sitting area or home office, a huge walk-in closet, and a spa-inspired bath with dual sinks and a glass-enclosed tile shower. Two additional generously sized bedrooms share a full bath with a tub/shower combo, while a third full bath with a walk-in shower provides added convenience for family or guests. Practicality meets comfort with a large indoor laundry room complete with folding space, plus a two-car side-entry garage with an epoxy floor. Sliding doors open to the fenced backyard with a covered patio—ideal for entertaining or enjoying Florida’s sunshine in peace. Recent updates include a new roof (2023), fresh interior paint, and a newer AC system, giving you peace of mind for years to come. All of this is in a prime Maitland location with quick access to I-4, highly rated schools (both public and private), and endless parks, trails, and activities. This home offers the lifestyle you’ve been waiting for—don’t miss the opportunity to make it yours!

955 Gamewell Avenue, Maitland
$255,000
Acreage & Unrec SubDv. ⋅ 32751 Zip Code
Lake Howell Rd with a Maitland city address. Build your home and professional office or mixed use such as office space and apartments above and live rent free. The city will allow up to approximately 3,700 sq ft of building area. You will not be able to find another opportunity like this close to everything: Semoran Blvd, restaurants, shopping and more!

Lake Howell Road, Maitland
$915,000
4 Beds ⋅ 3 Baths ⋅ Dommerich Hills SubDv. ⋅ 32751 Zip Code
One-story home in Dommerich Hills within walking distance to Dommerich Elementary and Maitland Middle schools. Move-in ready with wonderful pool. Beautifully landscaped.

2021 Chippewa Trail, Maitland
$335,000
2 Beds ⋅ 2 Baths ⋅ Branch Tree SubDv. ⋅ 32751 Zip Code
One or more photo(s) has been virtually staged. Welcome to this beautifully updated Branch Tree duplex, where style meets convenience! Step inside to discover a brand-new kitchen with sleek granite countertops and modern cabinetry, complemented by fresh paint throughout. The primary suite impresses with a fully renovated bathroom featuring a spacious walk-in shower and dual vanity. Luxury vinyl floors flow seamlessly through the open living spaces, highlighted by soaring ceilings that create a bright and airy atmosphere. Enjoy a private backyard for relaxing or entertaining, plus the convenience of a one-car garage. Perfectly situated near shopping, dining, UCF, and charming downtown Winter Park, this home offers both comfort and a prime location. Don’t miss your chance to make this move-in-ready gem yours!

419 Poplar Court, Maitland
$395,000
2 Beds ⋅ 2 Baths ⋅ Moorings On Lake Maitland Condo SubDv. ⋅ 32751 Zip Code
SELLER PAYING CONCESSIONS OF 6 MONTH HOA FEES. Something is very special about Lakefront Living! Come visit this beautiful Lakefront Condo located at The Moorings On Lake Maitland, part of the Winter Park chain of lakes. Enjoy the Florida lifestyle in a carefree home with lake front amenities. Imagine Entertaining Family & Friends at the Pool or Heated Spa and the Clubhouse of the Moorings on Lake Maitland. Enjoy relaxing on the Lake Front Dock or on your own Private Enclosed Patio! Step inside this spacious 2 bedroom 2 bath great room plan, perfect for relaxing or entertaining. The beautifully upgraded kitchen has stainless steel appliances and granite counters and a charming dining nook. The master suite features an updated ensuite bath with dual sinks and a walk in shower with a custom glass enclosure. There is a generous walk in closet with custom built ins. Imagine coffee in the morning with lake views from your living room or your spacious patio. Only 5 minute drive to Winter Park's shops & Sidewalk Dining along the famed Park Avenue. Stroll over to Maitland's lovely Lake Lilly Park for Seasonal Events, Art Festivals, Concerts and local Farmer's Market! Incredible Location & Lifestyle!!!!

204 Quayside Circle Unit 304, Maitland
$2,550,000
Hollieanna Shores 1st Add SubDv. ⋅ 32751 Zip Code
Wonderful lakefront lot opportunity to create a custom legacy estate on Lake Maitland, part of the Maitland-Winter Park Chain of Lakes. Lakefront homesites are becoming increasingly rare, and this offering is truly special. Tucked away on a quiet street, the property enjoys a very private setting with the ability to be gated, along with sweeping southern lake views that capture both sunrise and sunset in equal measure. Photos #9–#14 illustrate a thoughtfully conceived design concept created specifically to complement the lot’s dimensions and orientation, while maximizing panoramic lake views and indoor-outdoor living. With approximately 18,500 square feet of upland to be developed, there is potential to build a residence of approximately 7,500 square feet (roughly 40% of the lot size). The site has already been cleared and is ready for construction, allowing a future owner to move seamlessly from vision to reality. Property enhancements include a seawall, gated front entry drive, and a covered boat lift with dock—offering immediate access to boating, fishing, and water sports. This is a rare canvas for a multi-generational lakefront estate, where architectural distinction meets a lifestyle centered on the water. Days may be spent wakeboarding, casting a fishing line, or relaxing poolside as boats glide across the lake, while evenings invite effortless cruises across the water to the Winter Park Racquet Club for dinner, cocktails, and social gatherings. Nestled in a secluded enclave of Maitland, the property is just minutes from the boutiques and dining of Park Avenue, with convenient access to downtown Maitland, major roadways, and the greater Orlando area. Note: The adjacent lakefront property, 127 Whitecaps Circle (24,472 square feet, approximately 0.56 acres) is also listed for sale, presenting a rare opportunity to combine two neighboring lakefront parcels and create a private compound for family or friends. All building calculations and development potential to be confirmed with the City of Maitland and the buyer’s builder and architect during due diligence, as any referenced figures are preliminary and not officially verified.

125 Whitecaps Circle, Maitland
$178,900
2 Beds ⋅ 2 Baths ⋅ Cherrywood Gardens SubDv. ⋅ 32751 Zip Code
Welcome to Cherrywood Gardens! This charming 2-bedroom, 1.5-bath condominium offers 953 sq. ft. of comfortable living space in the heart of Maitland. Step inside to find an inviting living and dining room combo, a bright kitchen with included appliances, and a primary suite with a walk-in closet. Enjoy your mornings on the front porch or take advantage of the community’s amenities, including a pool & clubhouse. Association fees cover water, sewer, trash, exterior maintenance, and grounds upkeep—making for worry-free living. Located near top-rated schools, shopping, dining, and major roadways, this home provides both comfort and convenience. Whether you’re a first-time buyer, downsizing, or looking for an investment, this condo is a great opportunity to own in a desirable Maitland community.

107 Cherrywood Gardens Drive Unit 8, Maitland
$899,000
4 Beds ⋅ 3 Baths ⋅ Maitland Isle SubDv. ⋅ 32751 Zip Code
This beautifully updated residence, nestled on a desirable corner lot in the tranquil Maitland Isle Subdivision, offers nearly 2,900 square feet of refined living with four bedrooms and two and a half baths. The home enjoys private lake access to Lake Maitland on the Winter Park Chain of Lakes, combining natural beauty with everyday convenience. Designed with a split, open floor plan filled with abundant natural light, it showcases a completely renovated kitchen (2020) featuring a large island with granite countertops, wood cabinetry and stainless steel appliances. Upstairs, the spacious primary suite is a private retreat with its own balcony overlooking the pool and backyard, while the lushly landscaped grounds include mango, avocado and tangerine trees, creating a serene tropical escape. Recent updates elevate this home’s appeal, including new carpet (2025), a pool cleaner (2025), one A/C unit (2025), plantation shutters (2025), dishwasher (2025), new windows (2024), a car charger installation (2024), washing machine (2024) and attic insulation (2022). Additional enhancements include renovated baths, luxury vinyl plank flooring, updated exterior doors, outdoor fencing and energy-efficient solar panels (2018) that provide approximately $250 per month in electricity savings. The roof, pool equipment, and more have also been thoughtfully upgraded for peace of mind. Perfectly positioned within an excellent school district—Lake Sybelia Elementary, Maitland Middle and Winter Park High—this home is close to Maitland City Center, Park Avenue, and local dining, parks and recreation. Combining comfort, modern updates and an exceptional location, this Maitland Isle property is an outstanding opportunity in one of the area’s most sought-after neighborhoods.

121 Mariner Way, Maitland
$240,000
2 Beds ⋅ 1 Baths ⋅ Lake Maitland Terrace Apts SubDv. ⋅ 32751 Zip Code
One or more photo(s) has been virtually staged. Welcome to Lake Maitland Terrace, where lakeside living meets modern style! This beautifully updated first-floor condo offers comfort and convenience in one of Maitland’s most sought-after communities. Inside, you’ll find brand-new upgrades completed in 2025, including fresh flooring, a new water heater, and a new in-unit washer and dryer. The kitchen is a true highlight, featuring stainless steel appliances, quartz countertops, white shaker cabinets, a stylish backsplash, a center island, and a cozy breakfast nook that’s perfect for enjoying your morning coffee. Lake Maitland Terrace is all about lifestyle. Residents enjoy a lakefront pool and sundeck with stunning views of Lake Maitland, a clubhouse with Wi-Fi, a fully stocked kitchen, and a coffee bar. The community also offers a large dock for fishing or simply relaxing, boat slips for rent, kayak and paddleboard racks, shuffleboard, a putting green, and an enclosed bicycle garage. Additional conveniences include designated parking, gas grills by the pool, a car wash area, and on-site laundry facilities. Perfectly located, this condo is just minutes from local favorites like Eden Bar and the Enzian Theater, Luke’s Kitchen and Francesco’s, along with the Shoppes at Maitland and all the dining and boutiques of nearby Park Avenue. With its modern upgrades, resort-style amenities, and unbeatable location, this home is the perfect blend of comfort and Florida lakefront living. Don’t miss your chance to make it yours, schedule your private showing today!

1140 S Orlando Avenue Unit F2, Maitland
$285,000
3 Beds ⋅ 2 Baths ⋅ Hamlet At Maitland SubDv. ⋅ 32751 Zip Code
Welcome to 1073 Hamlet Drive—an updated 3-bedroom, 2-bathroom block home with over 1,000 square feet of comfortable living space, a 1-car garage, and a prime location in the highly sought-after community of Hamlet at Maitland. From the moment you step inside, you'll be greeted by vaulted ceilings, an abundance of natural light, and an open floor plan that’s ideal for entertaining. The spacious living room flows effortlessly to a sliding glass door that leads out to a cozy patio—perfect for summer BBQs and enjoying the Florida sunshine. The kitchen is well-appointed with stainless steel appliances, granite countertops, shaker-style cabinetry, and a dedicated food pantry for extra storage. The large owner’s suite offers a true retreat with its walk-in closet and en-suite bathroom featuring a dual-sink vanity with granite countertops, an oversized, well-lit mirror, and a garden tub with shower—perfect for soaking the day away. The home also includes a full guest bathroom and two additional guest bedrooms, one of which includes a walk-in closet. Situated in a friendly, owner-occupied community with a low HOA fee, Hamlet at Maitland places you near top-rated schools like Dommerich Elementary and Maitland Middle and just minutes from the best dining, shopping, and amenities of both Maitland and Winter Park. Schedule your private showing today—this one won't last!

1073 Hamlet Drive, Maitland
$552,000
4 Beds ⋅ 4 Baths ⋅ Dommerich Hills Fifth Add SubDv. ⋅ 32751 Zip Code
Distinctive Dommerich Hills Home with Flexible Floor Plan and Modern Upgrades. Welcome to this truly unique residence in the highly desirable Dommerich Hills neighborhood, where character, thoughtful updates, and a versatile layout come together to create the ideal setting for modern living. Perfectly situated just minutes from Winter Park and Maitland—and zoned for Dommerich Elementary, Maitland Middle, and Winter Park High—this home combines charm with convenience in one of Central Florida’s most sought-after locations. The spacious two-story design features four bedrooms plus a flexible bonus room, two full bathrooms, and two half baths. The main-level primary suite offers both privacy and comfort, complete with direct access to the backyard retreat. Upstairs, dual staircases provide easy flow to additional bedrooms and extensive hidden storage that spans the length of the home. The bonus room, outfitted with a Murphy bed and an adjacent half bath, is perfect for guests, a home office, or a fifth bedroom option. At the heart of the home, the chef’s kitchen is as functional as it is stylish, boasting gas appliances, butcher block counters with pop-up outlets, spice and oil niches, appliance hideaways, a pet nook, and a convenient pass-through window to the outdoor entertaining space. A butler’s pantry with beer and wine fridge, commercial-grade washer and dryer, and built-in bar elevate both everyday living and entertaining. Recent updates bring peace of mind: new roof (2022), HVAC (2019), windows (2021), garage door, tankless gas water heater, water softener, and new city sewer connection. Gas lines for the dryer, grill, or generator add extra efficiency. Outdoors, enjoy the Florida lifestyle in a private setting with a deck, gazebo, outdoor shower, and pergola-covered seating area. A private well feeds the irrigation system, keeping the landscaping lush year-round, while a cedar façade enhances curb appeal and architectural detail. This is not a cookie-cutter home—it’s a property designed for those who appreciate creativity, comfort, and functionality. With its top-rated schools, prime location, and a floor plan built for today’s needs, this Dommerich Hills treasure is a rare opportunity. Schedule your private showing today—homes like this don’t come along often.

1135 Thunder Trail, Maitland
$390,000
3 Beds ⋅ 2 Baths ⋅ Bucher Hgts SubDv. ⋅ 32751 Zip Code
Welcome! This well-maintained ranch-style home features a functional single-level design with a newer roof (2024) encompassing 1,523 square feet of living space, with an additional 255 square feet of expanded living space in the enclosed Florida Room to enjoy. The main living area includes three bedrooms and one and a half baths. a stunning kitchen (remodeled 2025), open floor plan, cozy Florida Room, and vinyl fenced backyard provide the perfect background to enjoy every day and a versatile space to accommodate your needs, and ideal for entertaining guests. Additional updates include a new HVAC system (2023), along with complete electrical rewiring featuring updated boxes, outlets, switches and fixtures. Location is a key advantage where convenience defines this neighborhood. Lake Sybelia Elementary is one block away, and primary services and a variety of shopping plazas are just minutes away, ensuring quick access to all your daily needs. For outdoor adventures, the Sandspur Bike Trail is also one block away, while Lake Sybelia and many other parks are close by, while Downtown Winter Park and the surrounding areas offer many quality choices for dining, entertainment, and shopping, providing a list of places to explore within a short distance. Quick access to I-4 makes commuting effortless, whether for work or exploring the greater Orlando area. This combination of recent improvements, desirable features, and prime location creates a prime opportunity just waiting for you. Schedule your private showing today to experience all that this beautiful home and location have to offer.

731 Bucher Road, Maitland
$507,200
3 Beds ⋅ 2 Baths ⋅ Coffins Sub SubDv. ⋅ 32751 Zip Code
Build Your Dream Home in Prime Maitland Location! A rare opportunity awaits at 1550 Ridgewood Avenue — located just steps from the Enzian Theater, Park Maitland School, and minutes from Whole Foods Market. Zoned for highly sought-after Dommerich Elementary, Maitland Middle, and Winter Park High School, this property offers the perfect foundation for your next custom build. With a lot size of 77' x 111' (and the potential to extend to 77' x 136'), this site provides flexibility and vision. Collect rental income from the existing home as you plan your future project. Whether you envision a luxury single-family residence or a high-end duplex, the possibilities are endless. This property is also listed as a pre-construction opportunity, with a preferred builder and architect already designing a one-of-a-kind custom home concept tailored for this parcel. Don’t miss the chance to create something exceptional in one of Central Florida’s most desirable locations.

1550 Ridgewood Avenue, Maitland
$361,200
4 Beds ⋅ 3 Baths ⋅ English Estates Unit 2 SubDv. ⋅ 32751 Zip Code
Discover potential in this spacious four-bedroom, three-bathroom home in the desirable English Estates area of Maitland. With original terrazzo floors hidden under the carpeting, a large living-dining room combination, and an updated kitchen that opens to the family room, featuring sliding glass doors to the covered patio and screened-in swimming pool, this property offers ample opportunity for a fresh new look. The large lot measures 75’ x 120’. Assigned public schools are English Estate Elementary, South Seminole Middle, and Lake Howell High School. This is truly a dream home for someone with the vision to transform it with care, or a savvy flipper seeking their next exciting project.

2570 Derbyshire Road, Maitland
$150,000
1 Beds ⋅ 1 Baths ⋅ Visconti West SubDv. ⋅ 32751 Zip Code
This third floor, 1 bedroom, 1 bathroom condo is located in the gated community of Visconti in Maitland near local shops, restaurants, schools, Maitland Boulevard, and I-4. Features include a spacious living room with vaulted ceilings, a lovely kitchen, a large bedroom with walk-in closet, laundry room, and balcony with a storage room. The Visconti community offers a variety of amenities to include a resort style swimming pool, clubhouse with business center, gym, basketball and tennis courts, a playground, and a car wash area.

1125 Lake Shadow Circle Unit 5305, Maitland
$825,000
4 Beds ⋅ 3 Baths ⋅ Wellington SubDv. ⋅ 32751 Zip Code
Welcome to your dream home in the friendly community of Wellington in Maitland. This impressive 4-bedroom, 3-bathroom residence spans 3,853 square feet and sits on a spacious 0.34-acre lot, perfect for family gatherings and entertaining. Step inside to discover an open layout filled with natural light. High ceilings and porcelain tile floors create an inviting atmosphere. The heart of the home, a gourmet kitchen, is equipped with stainless steel KitchenAid appliances, granite countertops, and a breakfast bar for casual dining. You'll love the convenience of two large pantries for all your cooking needs. The cozy family room has a beautiful fireplace and is open to the kitchen. The downstairs also includes a bedroom and bathroom perfect for in laws to stay the weekend! The upstairs includes the master suite, 2 additional bedrooms, another bathroom, a multi-function room perfect for movie night or workouts, and a well appointed laundry room. The master suite is a true retreat, showcasing a walk-in closet and a spa-like ensuite with a deep soaking tub and a spacious walk-in shower. It also features a large walk in closet, and an extra nook area for an office or nursery. Enjoy evenings on the sprawling patio, or cozy up by the fireplace indoors. Your outdoor oasis features a saltwater heated pool, a covered entertainment area, and a fire pit for memorable nights under the stars. The lush yard provides plenty of space for gardening and outdoor activities. Located near Kewannee Park, enjoy nature trails, playgrounds, and more, all within a quick bike ride. The nearby downtown Winter Park offers delightful dining and shopping. With easy access to I-4 and local attractions, this home is perfectly positioned for convenience. This family-friendly property includes SMART home features, energy-efficient windows, solar panels, and ample parking for your boat or RV. Come see how this spacious home can elevate your lifestyle.

1888 Derbyshire Road, Maitland
$310,000
3 Beds ⋅ 2 Baths ⋅ Thompson Sub SubDv. ⋅ 32751 Zip Code
Welcome to this beautifully renovated 3 bedroom, 2 bathroom home with 1,306 square feet of living space, perfectly situated on a spacious .15-acre lot in Maitland. From the moment you arrive, you’ll love the gorgeous curb appeal, manicured landscaping, and two-car garage. Step inside to find brand-new luxury vinyl plank flooring flowing throughout. The modern kitchen boasts stainless steel appliances, quartz countertops, and sleek finishes, making it the perfect space to gather and entertain. Each bedroom offers large windows, ceiling fans, and abundant natural light, while the updated bathrooms feature contemporary vanities and tile-lined showers for a spa-like feel. Enjoy the Florida lifestyle on the covered back porch overlooking the spacious backyard, ideal for hosting gatherings or simply relaxing at sunset. Living in Maitland means access to top-rated schools, beautiful parks, a vibrant dining scene, cultural attractions, and convenient proximity to Winter Park and downtown Orlando.

840 Mulberry Street, Maitland
$995,000
3 Beds ⋅ 3 Baths ⋅ Dommerich Woods SubDv. ⋅ 32751 Zip Code
BACK ON THE MARKET!! Welcome to 1630 Chinook Trail, a fully renovated custom patio-style home making its market debut. Designed by builder Phil Kerr and architect Alan Berman, this home features French doors from nearly every room opening to a sparkling pool. Inside you’ll find 3 bedrooms plus a den, guest suite with walk-in closet and ensuite bath, and a 4th bedroom converted into a spacious master closet that can easily be re-converted. The open floor plan boasts a chef’s kitchen with a 10-ft island, 2 dishwashers, double-wide fridge, double ovens with convection, pot filler, and gas range. Additional highlights include a gas fireplace, Nuvo sound system, tankless water heater, energy-efficient windows, and a 2-car garage with workshop space. Outdoors enjoy a travertine front patio, fenced backyard with deck and tree fort, and a resort-style pool with travertine decking and water feature. This home has deeded lake access and a private boat ramp into Lake Minnehaha and walking distance to top-rated schools and Maitland Community Park.

1630 Chinook Trail, Maitland
$375,125
3 Beds ⋅ 2 Baths ⋅ English Estates Unit 2 SubDv. ⋅ 32751 Zip Code
Welcome to 1241 Manchester Road, a spacious 3-bedroom, 2-bath home with over 2,000 sq ft of living space in the heart of Maitland. This solid block construction home, situated on a corner lot, offers incredible potential for new owners to bring their vision to life and make it their own. Inside, you’ll find generous living areas, a glassed Florida room, a breakfast nook adjacent the kitchen, a separate formal dining, family, and living/great room. Create the layout that suits your lifestyle best. With a newer roof and AC, much of the heavy lifting has already been done, leaving you free to focus on adding your personal touch. A quiet street in the desirable English Estates community, this property is ideal for those seeking a family home with character, comfort, and room to grow. An optional Homeowner’s Association offers a sense of community without the hefty fee. Don't miss the chance to transform this Maitland gem into your dream home!

1241 Manchester Rd, Maitland
$765,000
4 Beds ⋅ 3 Baths ⋅ Maitland Grove SubDv. ⋅ 32751 Zip Code
A fantastic 4-bedroom, 2.5-bath home with an office/flex space, located on a prime interior lot in the established Maitland Groves neighborhood. Major systems updated with a 40-year architectural roof (2013), Plumbing Re-pipe (2019); New windows and sliding doors (2023); Newer carpet in bedrooms; HVAC/AC (2006 with New Air Handler Blower Motor (Sept. 2025)), water heater (2008), and a whole-house generator (2008). Highlights include an open floorplan, cathedral ceilings, a cozy fireplace, and a spacious, updated island kitchen, white cabinetry with a breakfast nook. The large laundry/mudroom conveniently connects to an oversized side-entry 2-car garage, perfect for groceries and kids. A flex space overlooking the backyard offers great potential as an office, fitness area, or playroom. Both bathrooms feature double sink vanities, and the primary suite has sliding door access and views of the backyard. The property is landscaped for privacy, featuring a partially covered front entry courtyard and both open and covered patios in the backyard. Located in a top school district near Lake Sybelia Elementary, with easy access to parks, sport courts, bike paths, shopping, restaurants, a hospital, and the I-4 corridor.

380 White Oak Cir, Maitland
$939,000
5 Beds ⋅ 4 Baths ⋅ Dommerich Woods SubDv. ⋅ 32751 Zip Code
Under contract-accepting backup offers. Discover a rare opportunity in Dommerich Woods, a distinguished and established Maitland neighborhood celebrated for its rich heritage. Situated on .33 acre of lushly landscaped grounds, this remarkable property welcomes with paver drive and enjoys a tranquil setting along a peaceful creek connecting Lake Minnehaha and Lake of the Woods - creating an atmosphere of natural elegance and privacy. Re-roofed in 2023, this expansive 5 bedroom, 3 1/2 bath residence offers 4,144 HSF, and WHOLE HOUSE WATER SOFTNER, showcases a versatile TWO-LEVEL design, perfectly suited for refined living and gracious entertaining. The main level opens with a foyer leading into a bright, open living and dining area, where CEILING FANS throughout the main level add comfort and elegance. From here, step out onto the COVERED UPPER DECK with sweeping views of the SCREENED POOL, TROPICAL GARDEN, and serene backyard retreat - an ideal setting for morning coffee or evening gatherings. At the heart of the home, the GOURMET KITCHEN blends style and functionality with SOLID WOOD CABINETRY, a built-in WINE REFRIGERATOR and WINE RACK, granite countertops, and a CENTER ISLAND with SEATING, and REVERSE OSMOSIS WATER SYSTEM under the DOUBLE SINK. The adjacent laundry room offers exceptional storage, keeping household essentials organized. For added convenience , a two-car garage with built-in cabinets and workshop area, adjoins the spacious laundry room that has granite counters and washer and dryer. Also on the main level , adjacent to the primary bedroom with en-suite bath, a bedroom has been thoughtfully converted into a large closet featuring a CUSTOM CLOSET system, providing abundant space for wardrobe organization. Both levels feature inviting WOOD-BURNING FIREPLACES that add ambiance to the living spaces. On the lower level, a spacious family room, kitchenette, study/library/office, two bedrooms, full bath and half bath provide the perfect complement to easy living. Along the hallway, built-in wood shelving creates a refined showcase for books, art, or personal collections. While one bedroom includes a custom built in desk- ideal for work or study, a second bedroom adds flexibility for creative projects. This level opens onto the screened pool and patio area, designed for seamless indoor-outdoor living. Outside, tropical plantings, METERED IRRIGATION, and a winding private walkway leads along the soft murmur of the BORDERING CREEK. An added bonus is the storage room located below the kitchen which is approximately 375 sq.ft. Whether hosting guests or enjoying a quiet evening, this private oasis offers the ultimate backdrop for relaxed Florida living. Enjoy the opportunity to join the Dommerich Beach Civic Association with membership options including access to a private picnic area, boat ramp, canoe and kayak storage, and unforgettable evening sunsets. With its rare combination of design, flexible spaces, and an idyllic setting , this residence presents a unique opportunity to experience the very best of Maitland and Central Florida living. All this is convenient to some of Central Florida's finest schools, shopping, restaurants, parks, entertainment, businesses and more!

791 Sequoia Trail, Maitland
$1,655,000
5 Beds ⋅ 5 Baths ⋅ Lake Colony Ph 01 Rep SubDv. ⋅ 32751 Zip Code
Showpiece Charles Clayton Home in Gated Lake Colony Estates Every detail of this 5-bedroom, 4.5-bath plus office residence was designed to impress, including a full in-law apartment and an outdoor living space that feels like a private resort. Set on a prime corner lot, this home combines timeless craftsmanship with modern finishes: tile roof, travertine downstairs, hardwood upstairs, sleek wrought iron staircase, coffered ceilings, plantation shutters, and designer lighting. The chef’s kitchen is built for both cooking and entertaining—gas stove, double ovens, custom cabinetry, granite counters, oversized breakfast bar, and sunny dining nook. A two-sided stone fireplace connects the office and family room, adding warmth and character. The primary suite is a retreat of its own: spa-style shower with six body sprayers and dual rain heads, a private tankless water heater, and a two-story custom closet built for a true collection. Guests enjoy privacy with a separate stairway leading to a full in-law apartment complete with family room. Step outside to the ultimate backyard: screened, gas-heated pool, tongue-and-groove ceiling patio, outdoor kitchen with grill, sink, granite workspace, storage, TV, and built-in keg fridge. Additional highlights: spotless 3-car epoxy garage with workshop, built-in office cabinetry, 12-foot ceilings, beadboard accents, and a dog run. And the best part? All of this is in close proximity to Orangewood Christian School and just minutes from Winter Park, top-rated dining, and shopping. A rare opportunity to own a true Maitland showpiece.

104 E Lake Colony Drive, Maitland
$352,500
3 Beds ⋅ 2 Baths ⋅ N/A SubDv. ⋅ 32751 Zip Code
+++ AMAZING REHAB OPPORTUNITY IN MAITLAND WITH DEEDED LAKE ACCESS +++ HERE IS A GREAT CHANCE TO OWN IN BEAUTIFUL MAITLAND ON A STREET WITH ONLY 9 HOUSES, NO HOA, AND A BOAT RAMP (FOR RESIDENTS ONLY) ONTO 58 ACRE LAKE SEMINARY! PRICED WITH NEEDED RENOVATIONS IN MIND, THIS SOLID BLOCK HOME IS WAITING TO BE RETURNED TO PRISTINE CONDITION. MANY OF THE HOMES ON THIS STREET HAVE BEEN COMPLETELY RENOVATED. THIS HOME HAS 3 BEDROOM AND 2 FULL BATHS. THE KITCHEN AND UTILITY ROOM ARE LARGE AND ALL BEDROOMS ARE GOOD SIZE. THE LARGE FAMILY ROOM BOASTS A BRICK WOOD BURNING FIREPLACE. THE BACKYARD HAS A BEAUTIFUL IN-GROUND GUNITE AND CONCRETE POOL WITH THE ORIGINAL BRICK PAVER PATIO! HOME IS LOCATED MINUTES TO DOWNTOWN WINTER PARK AND I-4 RAMP.

106 Oakwood Drive, Maitland
$400,000
3 Beds ⋅ 2 Baths ⋅ Druid Hills Park SubDv. ⋅ 32751 Zip Code
Charming 3BR/2BA Home with Updated Interior This move-in ready home features 3 bedrooms, 2 bathrooms, and a bright open layout with stylish updates throughout. Enjoy fresh interior paint, updated flooring, and modern touches in both the kitchen and baths. The timeless exterior offers great curb appeal with fresh paint, dark shutters, and stone accents. A spacious backyard provides plenty of room for entertaining, gardening, or play, while the oversized driveway and attached two-car garage add convenience. Ideally located near schools, shopping, and local amenities, this home is perfect for first-time buyers or those looking to downsize but still want their privacy.

380 Banyan Drive, Maitland
$515,000
3 Beds ⋅ 4 Baths ⋅ Preserve At Maitland SubDv. ⋅ 32751 Zip Code
This home does more than check boxes. It tells a story. Minutes from downtown Winter Park, this modern residence offers the kind of design and layout that transforms daily routines into meaningful moments. Step inside to find tall ceilings, wide-plank wood floors, and a chef’s kitchen with quartz countertops, a gas range, and space to gather, cook, and connect. Each bedroom is a private suite with its own bathroom and custom closet system. A walk-in pantry, linen closet, dedicated laundry room, loft, and oversized two-car garage provide smart storage and flexibility. The floor plan supports both quiet mornings and lively evenings with room to grow, recharge, and entertain. Upstairs, the primary suite opens to a private balcony and a large patio perfect for a quiet coffee or a vibrant sunset gathering. The backyard is fully fenced and features premium LifeProof turf installed in November 2024. Outdoor outlets on both floors, a built-in gas line for grilling, and a paver patio create an ideal setup for open-air living. Recent upgrades include a roof, A/C, and water heater installed in 2020, along with a UVC light in the air handler to enhance air quality. The community offers access to Lake Howell Creek for fishing and kayaking, shared green space, and a low-maintenance lifestyle with a friendly neighborhood feel. With easy access to Park Avenue, major highways, restaurants, and shopping, this home is a refined blend of design, comfort, and location. It is ready for its next chapter.

2162 Lake Howell Preserve Court, Maitland
$1,035,000
4 Beds ⋅ 4 Baths ⋅ Maitland Club Rep SubDv. ⋅ 32751 Zip Code
A truly unique opportunity in the Maitland / Winter Park area, the Maitland Club community features a 24/7 guard-gated entrance for this executive home! This 4 BR, 3.5 BA home has all the features of a dream home, including a downstairs guest/in-law suite with private entry, a large front den for a home office, and a versatile bonus room ideal for a second office, gym, wine room, or hobby space. The renovated chef’s kitchen boasts wood cabinetry, granite counters, stainless steel appliances, an above-range pot filler, island seating, and a 6' x 6' walk-in pantry with custom shelving. Elegant finishes include wood floors throughout, plantation shutters, crown molding, and upgraded millwork. The family room features a cozy fireplace and offers beautiful views of the pool and mature backyard landscaping. The large primary suite showcases a seating area, custom walk-in closet, and remodeled bath with double vanities, beautiful tile work, new cabinetry, and even a window seat. The guest bedrooms on the second floor are generously sized with an updated Jack-and-Jill bath and custom storage solutions built into the closets. Enjoy a private backyard retreat with a resurfaced and heated pool featuring custom lighting, decorative tile, and a relaxing water feature, plus a covered patio and no rear neighbors. Upgrades are countless in this loved home, including ceiling storage and tool cabinets in the oversized 3-car garage, a new roof (2023), replumbed (2022), HVAC replacement (2022), new wood floors, custom closet built-ins, and even fresh paint. Community amenities include tennis, basketball, playground, and proximity to Orangewood PreK-12th grade School with quick access to Winter Park, I-4 Express, and all of Central Florida! Don't miss your chance to claim this dream custom home as your own!

904 Brightwater Circle, Maitland
$515,000
5 Beds ⋅ 2 Baths ⋅ English Estates Unit 1 SubDv. ⋅ 32751 Zip Code
Welcome to 1411 Glastonberry Road, a spacious 5-bedroom, 2-bathroom home tucked within the desirable English Estates community in Maitland. This established neighborhood is known for its tree-lined streets, sense of community, and highly sought-after location within the top-rated Seminole County Public School System, making it an excellent choice for those looking for both comfort and convenience. Step inside and you will find a thoughtfully designed split floorplan that maximizes space and privacy. The home has been updated with laminate flooring throughout, providing a modern look that is both stylish and low-maintenance. The bathrooms have been tastefully renovated, giving a fresh and contemporary feel that complements the home’s overall design. Essential updates have already been taken care of for you, a durable metal roof provides peace of mind for years to come, a complete re-plumb in 2021. One of the most notable features is that the home has been converted to public sewer! The heart of the home features open living and dining areas that flow seamlessly, creating the perfect setting for both everyday living and entertaining. With five bedrooms, there is ample flexibility for a growing household, guests, or even creating a home office or hobby room to suit your lifestyle needs. Outdoors, the home continues to impress with a spacious fenced backyard that offers plenty of room to play, garden, or simply relax in privacy. Enjoy evenings on the covered patio, or step out to the additional brick paver patio, an ideal spot for hosting barbecues, gatherings, or simply soaking up Florida sunshine. Location is key, and this property delivers. You are just a short 10–15 minute drive to Park Avenue in Winter Park, where you can enjoy upscale dining, boutique shopping, and cultural attractions. Easy access to major roadways ensures quick commutes to Downtown Orlando, the Maitland Business District, and surrounding areas, making this home as practical as it is inviting.

1411 Glastonberry Road, Maitland